The Comparative Nucleophilicity of Naphthoxide Derivatives in Reactions with a Fast-Red TR DyeCheryl M. MascarenhasIn this experiment, organic chemistry students perform reactions between three naphthyl acetate derivatives and the diazonium salt Fast-Red TR. Students discover under what conditions the hydrolysis and electrophilic aromatic substitution is fastest and slowest, allowing them to conclude that latter, rather than the former, is rate-limiting.Mascarenhas, Cheryl M. J. Chem. Educ.2008, 85, 1271.

Evaluating Mechanisms of Dihydroxylation by Thin-Layer ChromatographyBenjamin T. Burlingham and Joseph C. RettigPresents a microscale experiment in which cyclohexene is dihydroxylated under three sets of conditions and the products determined through thin-layer chromatography. Teams of students evaluate proposed mechanisms for each dihydroxylation in light of the data collected.Burlingham, Benjamin T.; Rettig, Joseph C. J. Chem. Educ.2008, 85, 959.

The Preparation and Enzymatic Hydrolysis of a Library of EstersElizabeth M. Sanford and Traci L. SmithIn this investigative case study, students work collaboratively to prepare and characterize a library of esters using Fischer esterification and alcoholysis of acid chlorides and their subsequent enzymatic hydrolysis by pig liver and orange peel esterases.Sanford, Elizabeth M.; Smith, Traci L. J. Chem. Educ.2008, 85, 944.

Drugs / Pharmaceuticals |

Enzymes |

Esters |

Industrial Chemistry |

IR Spectroscopy |

NMR Spectroscopy |

Synthesis |

Thin Layer Chromatography

The Resolution of Ibuprofen, 2-(4′-Isobutylphenyl)propionic AcidJames V. McCullaghIn this experiment the over-the-counter pain reliever ibuprofen is resolved using (S)-(-)-a-phenethylamine as the resolving agent. This procedure has several key advantages over previous resolution experiments.McCullagh, James V. J. Chem. Educ.2008, 85, 941.

Chirality / Optical Activity |

Drugs / Pharmaceuticals |

Enantiomers |

Quantitative Analysis |

Separation Science

If You Were a Molecule in a Chromatography Column, What Would You See?John MatticeTo visualize what takes place in a chromatography column, enlarge the molecules to human size and expand the columns to keep the ratio of size of molecule to size of column the same. Using such a model, this article explains how band broadening occurs as a result of resistance to mass transfer, multiple flow paths, and stagnant mobile phase.Mattice, John. J. Chem. Educ.2008, 85, 925.

Converting Municipal Waste into Automobile Fuel: Ethanol from NewspaperMark Mascal and Richard ScownIn this experiment, waste newspaper is pulped with acid and its cellulose hydrolyzed to produce glucose syrup that is fermented and distilled to yield ethanol. In doing so, students are introduced to carbohydrate chemistry and the use of fermentation in organic synthesis.Mascal, Mark; Scown, Richard. J. Chem. Educ.2008, 85, 546.

A Simple Method for Drawing Chiral Mononuclear Octahedral Metal ComplexesAminou Mohamadou and Arnaud HaudrechyThis article presents a simple and progressive method to draw all of the octahedral complexes of coordination units with at least two different monodentate ligands and show their chiral properties.Mohamadou, Aminou; Haudrechy, Arnaud. J. Chem. Educ.2008, 85, 436.

Asymmetric Synthesis |

Chirality / Optical Activity |

Coordination Compounds |

Diastereomers |

Enantiomers |

Molecular Properties / Structure |

Stereochemistry |

Transition Elements

Synthesis of Quaternary Ammonium Salts of Tricyclic Cationic Drugs: A One-Pot Synthesis for the Bioorganic Chemistry LaboratoryLinda S. Brunauer, Abid C. Mogannam, Won B. Hwee, and James Y. ChenDescribes a one-pot conversion of tricyclic cationic drugs to their quaternary ammonium forms for a widely used bioactive drug, chlorpromazine, a phenothiazine-based antipsychotic. The conversion of parent drug to the methylated form was evaluated by qualitatively measuring its ability to induce alterations in the shape of mammalian erythrocytes.Brunauer, Linda S.; Mogannam, Abid C.; Hwee, Won B.; Chen, James Y. J. Chem. Educ.2007, 84, 1992.

Synthesis of Anomeric Methyl Fructofuranosides and Their Separation on an Ion-exchange ResinErkki Nurminen, Päivi Poijärvi, Katja Koskua, and Jari HovinenTreatment of d-fructose with methanol in the presence of acid as a catalyst gives a mixture of methyl--d-fructopyranoside, methyl-a-D-fructofuranoside, and methyl--d- fructofuranoside, which are separated on an ion exchange column and characterized polarimetrically.Nurminen, Erkki; Poijärvi, Päivi; Koskua, Katja; Hovinen, Jari. J. Chem. Educ.2007, 84, 1480.

Isolation of Three Components from Spearmint Oil: An Exercise in Column and Thin-Layer ChromatographyDon R. Davies and Todd M. JohnsonIn this exercise, the three major components of spearmint oil, (+)-limonene, L-(-)-carvone, and (1R,2R,4R)-dihydrocarveol, are separated by silica gel column chromatography. The separation is monitored by thin-layer chromatography, and IR analysis is employed to verify the identity of the separated components.Davies, Don R.; Johnson, Todd M. J. Chem. Educ.2007, 84, 318.

Precision in Stereochemical TerminologyLeRoy G. Wade, Jr.This article recommends that instructors use the precise terms asymmetric carbon atom and chirality center when they apply, and use the broader term stereocenter only when there is a need to include stereogenic atoms that are not chirality centers.Wade, LeRoy G., Jr. J. Chem. Educ.2006, 83, 1793.

Chemical Technicians |

Diastereomers |

Enantiomers |

Stereochemistry |

Nomenclature / Units / Symbols |

Chirality / Optical Activity

An Inexpensive Device for Capillary Electrophoresis with Fluorescence DetectionGreg Anderson, Jonathan E. Thompson, and Khriesto ShurrushDescribes an inexpensive device for performing capillary electrophoresis separations with fluorescence detection. As a demonstration of utility, the device is used to determine the mass of riboflavin in a commercially available dietary supplement.Anderson, Greg; Thompson, Jonathan E.; Shurrush, Khriesto. J. Chem. Educ.2006, 83, 1677.

Calix[4]pyrrole: Synthesis and Anion-Binding Properties. An Organic Chemistry Laboratory ExperimentJames A. Shriver and Scott G. WestphalSimple calixpyrrole macrocycles provide an easy-to-synthesize example of an anion-binding agent that can be included in the undergraduate laboratory curriculum. The inclusion of a test for anion binding also makes this procedure suitable for a more advanced audience and supplies a bridge for the introduction of supramolecular chemistry and a typical hostguest interaction. Shriver, James A.; Westphal, Scott G. J. Chem. Educ.2006, 83, 1330.

A Greener Approach to Aspirin Synthesis Using Microwave IrradiationIngrid Montes, David Sanabria, Marilyn García,, Joaudimir Castro, and Johanna FajardoPresents an inquiry-based laboratory experience based on the use of a microwave oven as a means for a comparative study of the effect of different catalysts in the synthesis of aspirin. Montes, Ingrid; Sanabria, David; García,, Marilyn; Castro, Joaudimir; Fajardo, Johanna. J. Chem. Educ.2006, 83, 628.

Just Click It: Undergraduate Procedures for the Copper(I)-Catalyzed Formation of 1,2,3-Triazoles from Azides and Terminal AcetylenesWilliam D. Sharpless, Peng Wu, Trond Vidar Hansen, and James G. LindbergIn keeping with the defining aspects of click chemistry, this reaction is high-yielding, requires no chromatography, is easily monitored by TLC, and displays distinct peaks in both IR and 1H-NMR. Virtually all products precipitate, and with just a few different starting blocks, every student, or pair of lab partners, can produce a unique "clicked" compound.Sharpless, William D.; Wu, Peng; Hansen, Trond Vidar; Lindberg, James G. J. Chem. Educ.2005, 82, 1833.

Monoterpene Unknowns Identified Using IR, 1H-NMR, 13C-NMR, DEPT, COSY, and HETCORLisa T. AltyThis set of NMR experiments can be a capstone experience for a spectroscopy or advanced laboratory course following organic chemistry. Students are given a monoterpene to identify using IR, 1H-NMR, 13C-NMR, and DEPT data. Once the unknown is identified, they can fully interpret and assign each carbon and each proton signal to the structure using COSY and HETCOR along with the one-dimensional NMR data. The rigidity of the ring systems and the chiral centers in all of the compounds present diastereotopic hydrogens and, in some cases, diastereotopic methyl groups. Alty, Lisa T. J. Chem. Educ.2005, 82, 1387.

Natural Products |

NMR Spectroscopy |

Diastereomers |

Chirality / Optical Activity |

IR Spectroscopy |

Undergraduate Research

Cis and Trans Isomers of CycloalkenesSusan E. Barrows and Thomas H. EberleinThe purpose of this article is to provide that analysis. In order for a cycloalkene to accommodate a trans double bond one or more of the following nonideal geometries must occur: a twisted p bond; pyramidal sp2-carbon atoms; nonideal sp3 bond angles; or longer than normal CC single and double bonds. This article provides a list of experimentally determined relative energies of the cis and trans isomers within the series cycloheptenecycloundecene, along with computationally derived energies at several levels of theory. It also examines the geometric distortions through which cycloalkenes relieve the strain introduced by a trans double bond. Barrows, Susan E.; Eberlein, Thomas H. J. Chem. Educ.2005, 82, 1334.

Computational Chemistry |

Molecular Modeling |

Alkenes |

Diastereomers

Ewing's Analytical Instrumentation Handbook, 3rd Edition (Jack Cazes)Jack K. SteehlerThis resource is a figurative and literal heavyweight. Its 31 chapters and more than 1000 large-size pages (filled with small text) provide an enormous amount of information. About a third of the book discusses spectroscopic techniques (11 chapters, all the standard types of spectroscopy); the second third covers various separation methods (10 chapters); and the remaining third hits a cross section of other topics, including four chapters on electrochemistry and three chapters on automation. The core of spectroscopy and separation science is appropriate and well chosen, covering the expected topics. There is even a chapter on Validation of Chromatographic Methods, an important topic for any lab working in a regulated environment. Additional, more unusual chapters include a chapter on Chiroptical Spectroscopy and a long chapter (100 pages) on Microfluidic Lab-on-a-Chip methods, both of current research interest.Steehler, Jack K. J. Chem. Educ.2005, 82, 1315.

Atomic Spectroscopy |

Bioanalytical Chemistry |

Chromatography |

Electrochemistry |

Electrophoresis |

EPR / ESR Spectroscopy |

Gas Chromatography |

HPLC |

Instrumental Methods |

Separation Science |

Spectroscopy

Capillary Electrophoresis Analysis of Substituted Benzoic Acids. An Experiment for the Organic Synthesis LaboratoryNancy S. Mills, John D. Spence, and Michelle M. BusheyWe have introduced an experiment into the organic chemistry sequence, in the synthesis laboratory, that utilizes capillary electrophoresis to evaluate the pKa shift on a series of student-prepared substituted benzoic acids. The pKa shift is examined in reference to the electrophoretic-migration behavior of benzoic acid and is a result of the electron-withdrawing or electron-donating characteristics of the substituent. This strategy allows us to increase the exposure of students to modern methods of separation. We are using repeated exposure to increase students' knowledge of separation strategies and techniques. Mills, Nancy S.; Spence, John D.; Bushey, Michelle M. J. Chem. Educ.2005, 82, 1226.

Synthesis |

Electrophoresis |

Grignard Reagents |

Instrumental Methods |

Separation Science

The Addition of Bromine to 1,2-Diphenylethene Judith C. Amburgey-Peters and LeRoy W. HaynesWe investigated the reaction of (Z)-1,2-diphenylethene (cis-stilbene) with various brominating reagents and solvents following directions in standard organic chemistry manuals. We were particularly interested in learning which combination of brominating reagent and solvent gave the best yield of (d,l)-1,2-dibromo-1,2-diphenylethane without the formation of significant amounts of meso-1,2-dibromo-1,2-diphenylethane, which is essentially the sole product from the reaction of bromine with (E)-1,2-diphenylethene (trans-stilbene). Based on the results from the standard preparatory methods, some permutations of solvent and brominating reagent were tried.Amburgey-Peters, Judith C.; Haynes, LeRoy W. J. Chem. Educ.2005, 82, 1051.

Addition Reactions |

Alkenes |

Carbocations |

Diastereomers |

Enantiomers |

Mechanisms of Reactions |

Stereochemistry

An Engaging Illustration of the Physical Differences among Menthol StereoisomersEdward M. Treadwell and T. Howard BlackThe differences and similarities in the physical behavior of enantiomers and diastereomers can easily be demonstrated using the commercial stereoisomers (-)-menthol, (+)-menthol, (+)-isomenthol, and (+)-neomenthol. Thin-layer chromatography and melting point determinations clearly show that diastereomers have different physical properties from enantiomers and each other, but that enantiomers have identical physical properties in achiral environments. By obtaining a mixed melting point and optical rotations the difference in enantiomers can be observed.Treadwell, Edward M.; Black, T. Howard. J. Chem. Educ.2005, 82, 1046.

Pharmaceutical Applications of Ion-Exchange ResinsDavid P. ElderThe historical uses of ion-exchange resins and a summary of the basic chemical principles involved in the ion-exchange process are discussed. Specific applications of ion-exchange resins are provided. The utility of these agents to stabilize drugs are evaluated. Commonly occurring chemical and physical incompatibilities are reviewed. Elder, David P. J. Chem. Educ.2005, 82, 575.

Drugs / Pharmaceuticals |

Ion Exchange |

Natural Products |

Separation Science

Separation and Determination of Cr(III) and Cr(VI) with Cation-Exchange Chromatography and Atomic Absorption Spectroscopy. An Experiment for Quantitative Methods of AnalysisAli Bazzi, Bette Kreuz, James Wuokila, and Ahmed MaqboulThis article reports on the separation and determination of Cr(III) and Cr(VI) with cation-exchange chromatography and flame atomic absorption spectroscopy. A sample containing the two ions is added to a column containing a cation-exchange resin; the Cr(VI) ions are not retained by the resin and are collected in the effluent. The Cr(III) ions are retained by the resin and eluted with an HCl solution. The separated ions are aspirated into an air/acetylene flame and the absorbance measurements are made at 357.9 nm and 0.2-nm slit width. The experiment has been implemented in a quantitative methods of analysis course.Bazzi, Ali; Kreuz, Bette; Wuokila, James; Maqboul, Ahmed. J. Chem. Educ.2005, 82, 435.

Atomic Properties / Structure |

Ion Exchange |

Quantitative Analysis |

Separation Science |

Chromatography |

Atomic Spectroscopy

Fractional Distillation of Air and Other Demonstrations with Condensed GasesMaria Oliver-Hoyo and William L. Switzer, IIIThis demonstration builds upon the commonly performed liquefaction of air not only to show the presence of nitrogen and oxygen, but also the presence of two other components, carbon dioxide and water. Several extensions are suggested: one to show boiling point elevation in solution and another to show the elevation of both boiling point and sublimation point with pressure. No special apparatus is required permitting presentations to audiences in a variety of settings. These demonstrations give the opportunity to discuss properties of gases, solution chemistry, and phase equilibria.Oliver-Hoyo, Maria; Switzer, William L., III. J. Chem. Educ.2005, 82, 251.

M&M OrangeJohn W. ElderThe article A New Glow on the Chromatography of M&M Candies was of interest to us as we had run a similar experiment using Kool-Aid dyes for some time. Last year we included this experiment in our organic labs on chromatography with considerable success. But I was intrigued by the identity of the unidentified orange listed in the supplementary material as being found in orange and brown M&Ms.Elder, John W. J. Chem. Educ.2005, 82, 209.

Chromatography |

Separation Science |

Dyes / Pigments |

Food Science |

Consumer Chemistry

Checkerboard ChromatographyCharles A. SmithThis hands-on activity allows students to simulate chromatographic simulations using a grid, colored pieces of paper, and a six-sided die. Students observe the separation as it is occurring and perform experiments on flow rate, column length, and mobile phase composition.Smith, Charles A. J. Chem. Educ.2004, 81, 384A.

Chromatography |

Instrumental Methods |

Separation Science

Capillary Electrophoresis Analysis of Cations in Water Samples. An Experiment for the Introductory LaboratoryChristopher J. Pursell, Bert Chandler, and Michelle M. BusheyThis experiment can be done in a lab, as a "dry-lab", or as an in-class exercise. Students explore a number of basic separation topics and work with figures of merit for real and meaningful samples. We have adopted a strategy where students encounter various instruments and methods of analyses multiple times throughout the curriculum. The level of sophistication in the exposures increases with the experience level of the students. Through this repeated exposure students will gain a better and fuller understanding of these methods than they would with a single exposure to the technique in the analytical or instrumental laboratory. Pursell, Christopher J.; Chandler, Bert; Bushey, Michelle M. J. Chem. Educ.2004, 81, 1783.

Electrophoresis |

Quantitative Analysis |

Separation Science |

Chemometrics |

Water / Water Chemistry

Application of Ion Chromatography to the Investigation of Real-World SamplesRebecca J. Whelan, Theresa E. Hannon, David J. Rakestraw, and Richard N. ZareAn experiment using ion chromatography in an undergraduate analytical chemistry laboratory is described. The students, working in small groups, are responsible for identifying a real-world system of interest and for developing a strategy to investigate that system. The students gain specific skills and knowledge about chromatography as well as more general analytical skills including sample preparation, system calibration, determination of detection limits, and data analysis. Two specific examples of experiments done by students in the class are presented: the determination of lead in hair dye and the determination of anions in orange juice. Whelan, Rebecca J.; Hannon, Theresa E.; Rakestraw, David J.; Zare, Richard N. J. Chem. Educ.2004, 81, 1299.

Chromatography |

Consumer Chemistry |

Dyes / Pigments |

Food Science |

Ion Exchange |

Quantitative Analysis |

Separation Science

A Computer-Based Undergraduate Exercise Using Internet-Accessible Simulation Software for the Study of Retention Behavior and Optimization of Separation Conditions in Ion ChromatographyPaul R. Haddad, Matthew J. Shaw, John E. Madden, and Greg W. DicinoskiAn ion chromatography exercise is described that uses a free Internet-based software package, Virtual Column 2, to simulate retention behavior and to optimize separation conditions. Virtual Column 2 permits the detailed study of retention behavior of inorganic anions on a Dionex AS11 column using isocratic hydroxide eluents and also on a Dionex AS4ASC column using carbonate-bicarbonate eluents. Collection of retention data from Virtual Column 2 allows students to investigate the effects of variation in eluent composition on retention, to examine separation selectivity in ion chromatography, and to evaluate the performance of simple retention models.Haddad, Paul R.; Shaw, Matthew J.; Madden, John E.; Dicinoski, Greg W. J. Chem. Educ.2004, 81, 1293.

Instrumental Methods |

Ion Exchange |

Separation Science |

Water / Water Chemistry

The History of Ion Chromatography: The Engineering PerspectiveBarton EvansThis article traces the history of the engineering development related to the several generations of ion chromatography instruments, columns, suppressers, and software. In so doing, several representative engineering challenges and their outcomes are discussed including: early directions (traveling without a road map, or "going where the applications are"), dealing with an extremely corrosive mobile phase (aka: the "eluent"), resolving the inherent incompatibilities of nonmetallic flow paths with the benefits of high-pressure, elevated temperature operation, managing the ever-evolving nature of the suppressor, coping with requirements for ultra high-end online systems, and providing extremely simple-to-use dedicated analyzer systems. Evans, Barton. J. Chem. Educ.2004, 81, 1285.

Chromatography |

Industrial Chemistry |

Instrumental Methods |

Ion Exchange |

Laboratory Equipment / Apparatus |

Separation Science |

Water / Water Chemistry

Ion Chromatography: An Account of Its Conception and Early DevelopmentHamish SmallIn the late 1950s, a small group of chemists at the Dow Chemical Company envisioned replacing these classical methods of inorganic analysis with but a single, universal chromatographic technique. They called their project "Inorganic Chromatography". This article describes how they developed this concept into a new technique, ready for commercial development into what we know today as "Ion Chromatography". In particular, the account will describe: how the Dow scientists adapted electrical conductance monitoring to chromatography, the introduction of the suppressor to chromatography, the invention of special stationary phases, and the evolution of strategies and principles that would shape and guide the practice of ion chromatography for many years to come. Small, Hamish. J. Chem. Educ.2004, 81, 1277.

Novel Strategies for the Removal of Toxic Metals from Soils and WatersD. Max RoundhillThis article surveys the toxicities of mercury, cadmium, lead, copper, cadmium, and the actinides. Strategies for the removal of these metals include surfactants, aqueous biphasic systems, and liquid membranes. For soils, both in situ stabilization and detection are discussed. Roundhill, D. Max. J. Chem. Educ.2004, 81, 275.

The Separation and Identification of Two Unknown Solid Organic Compounds: An Experiment for the Sophomore Organic Chemistry LaboratoryPatty L. FeistStudents are given a mixture of a solid ketone and a solid alcohol and asked to separate and identify the two components. First the students use TLC to determine the optimum solvent system to separate the two compounds, then they separate the unknowns on a microscale flash chromatography column. The students acquire the melting point, and if possible, the IR and 1H NMR spectra for each separated compound and identify them by matching the observed data with that of known compounds. Feist, Patty L. J. Chem. Educ.2004, 81, 109.

Chromatography |

IR Spectroscopy |

Microscale Lab |

NMR Spectroscopy |

Separation Science |

Qualitative Analysis

Manual Microscale Column Chromatography Pressurization ApparatusBruce W. BaldwinPressurization of a Pasteur pipet for microscale chromatography is simplified by connecting a 20- or 30-mL syringe to the pipet using a length of Tygon tubing. This simple system allows the student to easily dry-pack a column using common chromatography packing materials. Baldwin, Bruce W. J. Chem. Educ.2003, 80, 1182.

Safe and Efficient Flash Chromatography Equipment for the Research/Teaching LabFritiof Pontén and Ulf EllervikA new method for performing flash chromatography is presented in which the solvent reservoir is at the side of the column, in a separate bottle, connected with a Teflon tube to an adapter for standard flash chromatography columns. Pontén, Fritiof; Ellervik, Ulf. J. Chem. Educ.2001, 78, 363.

The Escalator--An Analogy for Explaining Electroosmotic FlowAndrew J. Vetter and Garrett J. McGowanAn analogy of people on an escalator for teaching the concept of electroosmotic flow. The moving escalator is analogous to the overall bulk flow of solution through the capillary (electroosmotic flow) and partly responsible for the separation of species using capillary electrophoresis (CE). Vetter, Andrew J.; McGowan, Garrett J. J. Chem. Educ.2001, 78, 209.

Instrumental Methods |

Separation Science |

Electrophoresis |

Transport Properties |

Electrochemistry

Fast Ionic Migration of Copper ChromateAdolf CortelAmong the many demonstrations of ionic migration in an electric field, the ones showing the migration of colored Cu+2 and CrO4-2 ions are popular. The demonstration described here introduces some modifications to allow a fast displacement of these ions.Cortel, Adolf. J. Chem. Educ.2001, 78, 207.

Practical Capillary Electrophoresis, 2nd Edition by Robert WeinbergerLuanne TilstraOverview of how capillary electrophoresis (CE) is unique, a history of technique development, a list of commercially available instruments, the basic concepts that one must understand to design and understand a CE experiment, and other reference information of significance to CE.Tilstra, Luanne. J. Chem. Educ.2001, 78, 35.

Elucidation of Molecular Structure Using NMR Long-Range Coupling: Determination of the Single Isomer Formed in a Regiospecific ReactionSamuel Delagrange and Françoise NepveuThe experiment presented in this article introduces students to the main concepts of two essential NMR techniques for investigating molecular structure. Heteronuclear multiple bond connectivity (HMBC) and proton-coupled 13C NMR are used to determine which isomer, from a possible two, is formed by a regiospecific reaction. The demonstration, based on long-range coupling between quaternary carbons and protons on neighboring carbons, is presented step by step. Delagrange, Samuel; Nepveu, Françoise. J. Chem. Educ.2000, 77, 895.

Rapid, Simple Quantitation in Thin-Layer Chromatography Using a Flatbed ScannerMitchell E. JohnsonSimply scanning a visibly stained TLC plate into a computer substitutes for much more expensive plate readers. With common image analysis software, "elution" profiles can be obtained. The resulting "chromatograms" can be analyzed in the same manner as other chromatograms. Johnson, Mitchell E. J. Chem. Educ.2000, 77, 368.

Isolation of Curcumin from TurmericAndrew M. Anderson, Matthew S. Mitchell, and Ram S. MohanThe active ingredient in turmeric is curcumin, which is approximately 2% by weight of the root of turmeric. We have developed two simple procedures for isolation of curcumin from turmeric, making this a new and interesting natural product isolation experiment. Anderson, Andrew M.; Mitchell, Matthew S.; Mohan, Ram S. J. Chem. Educ.2000, 77, 359.

Chromatography |

Medicinal Chemistry |

Natural Products |

Synthesis |

Separation Science |

Aromatic Compounds

Introducing Chiroscience into the Organic Laboratory CurriculumKenny B. Lipkowitz, Tim Naylor, and Keith S. Anliker"Chiroscience" is a young but robust industry linking science and technology with chemistry and biology; includes description of an asymmetric reduction of a ketone followed by an assessment of the enantiomeric excess by GC using a chiral stationary phase.Lipkowitz, Kenny B.; Naylor, Tim; Anliker, Keith S. J. Chem. Educ.2000, 77, 305.

Chirality / Optical Activity |

Chromatography |

Mechanisms of Reactions |

Synthesis |

Separation Science |

Stereochemistry |

Gas Chromatography |

Aldehydes / Ketones

Undergraduate Separations Utilizing Flash ChromatographyGail HorowitzThis article describes the procedures used to carry out four flash chromatography experiments: the isolation of the carotenes, chlorophylls and xanthophylls from a spinach extract; the separation of -carotene from tetraphenyl cyclopentadienone; the isolation of (+) and (-) carvone from caraway and spearmint oil; and the purification of benzil from benzoin. Horowitz, Gail. J. Chem. Educ.2000, 77, 263.

Separation and Quantification of Simple Ions by Capillary Zone ElectrophoresisMary BoyceA wide range of samples can be rapidly separated and quantified by CE, requiring only small amounts of sample and solvent. The experiments described here give a suitable introduction to capillary electrophoresis and effectively illustrate the mechanism of separation. Boyce, Mary. J. Chem. Educ.1999, 76, 815.

Instrumental Methods |

Separation Science |

Electrophoresis |

Chromatography |

Quantitative Analysis

A Way To Predict the Relative Stabilities of Structural IsomersJohn M. LyonThis paper discusses a method to evaluate the relative stabilities of structural isomers of inorganic and organic compounds. The method uses a simple set of rules that can be applied with only a knowledge of the electron configuration of the atoms and the periodic trends in atomic size.Lyon, John M. J. Chem. Educ.1999, 76, 364.

Covalent Bonding |

Diastereomers |

Molecular Properties / Structure

Chemistry of the Heaviest Elements-One Atom at a TimeDarleane C. Hoffman and Diana M. LeeA 75-year perspective of the chemistry of the heaviest elements, including a 50-year retrospective view of past developments, a summary of current research achievements and applications, and some predictions about exciting, new developments that might be envisioned within the next 25 years.Hoffman, Darleane C.; Lee, Diana M. J. Chem. Educ.1999, 76, 331.

Chromatography |

Instrumental Methods |

Isotopes |

Nuclear / Radiochemistry |

Separation Science |

Descriptive Chemistry |

Enrichment / Review Materials |

Atomic Properties / Structure

Student Understanding of Chromatography: A Hands-On ApproachRobert D. Curtright, Randy Emry, and John Markwell*This exercise sets up a collaborative activity that challenges students to develop a chromatographic solvent with the appropriate polarity to separate leaf chlorophyll and anthocyanin pigments by TLC. The suggested activity has been tested with both high-school advanced-chemistry students and with undergraduate students in an introductory biochemistry class. Curtright, Robert D.; Emry, Randy; Markwell, John. J. Chem. Educ.1999, 76, 249.

Chromatography |

Natural Products |

Separation Science |

Undergraduate Research |

Thin Layer Chromatography

The Preparation of a Fluorescent Dye: A Microscale TLC ExperimentDaniel S. Calimente, Shannon M. Strand, Shao-Chieh Chang, and David E. LewisThis paper describes an experiment that allows the instructor to introduce TLC as a technique for analyzing reaction mixtures by monitoring the formation of a fluorescent dye. The experiment also illustrates the effects of eluting solvent on elution order. Calimente, Daniel S.; Strand, Shannon M.; Chang, Shao-Chieh; Lewis, David E. J. Chem. Educ.1999, 76, 82.

Stereowordimers-Minding Your P's and Q'sEdward G. NeelandThe use of words having different colored sides is a excellent way to introduce stereochemical concepts that might not be easily grasped when using molecular examples. We have found that concepts such as enantiomers, diastereomers, identical molecules, chirality, achirality, mirror planes of symmetry, and internal planes of symmetry are readily understood by students when using stereowordimer examples.Neeland, Edward G. J. Chem. Educ.1998, 75, 1573.

Stereochemistry |

Diastereomers |

Enantiomers |

Molecular Properties / Structure

A Simplified Method for the Microscale Extraction of Pigments from SpinachKimberley R. Cousins and Kathleen M. PiersonA method is presented for microscale sample preparation for the thin-layer chromatographic analysis of the pigments in spinach. A commercial vegetable juicer is used for the initial extraction from spinach. This is followed by filtration, liquid/liquid extraction, centrifugation, and evaporation. Cousins, Kimberley R.; Pierson, Kathleen M. J. Chem. Educ.1998, 75, 1268.

Chromatography |

Microscale Lab |

Plant Chemistry |

Dyes / Pigments |

Thin Layer Chromatography |

Separation Science

Chromatographic Separation Techniques for UndergraduatesDarwin B. Dahl, John T. Riley, and Thomas K. GreenOver the past several years the Chemistry Department at Western Kentucky University (WKU) has sought to strengthen its undergraduate program departmental through acquisition of FT-NMR, fluorescence, electrochemical, thermal analysis, laser Raman, microscale organic, and polymer laboratory instrumentation; this has enabled the department to build a successful undergraduate program. Dahl, Darwin B.; Riley, John T.; Green, Thomas K. J. Chem. Educ.1998, 75, 1209.

Separation Science |

Chromatography |

Fourier Transform Techniques |

NMR Spectroscopy |

Raman Spectroscopy |

Electrochemistry |

Photochemistry |

Thermal Analysis |

Microscale Lab

An Inexpensive Detector for Gas ChromatographyAllan L. Smith, Edward J. Thorne, and Wolfgang NadlerWe have developed a low-cost (parts cost approximately $70) detector that can be used in a freshman level class to demonstrate the fundamental principles of gas chromatography (GC). The detector box can be used in a modification of experiments available in the literature which do not enable a quantitative method of analysis. We have used it with success in a freshman class of approximately 450 students in an experiment to separate chlorinated hydrocarbons via GC. Smith, Allan L.; Thorne, Edward J.; Nadler, Wolfgang. J. Chem. Educ.1998, 75, 1129.

Laboratory Equipment / Apparatus |

Gas Chromatography |

Separation Science

Capillary Electrophoresis in the Analytical and Physical Chemistry LaboratoriesKathryn R. WilliamsAvailability of capillary electrophoresis (CE) instrumentation allows students to have hands-on experience with this modern separation tool. They gain more than operational knowledge, however. Inherent in the instructional process is an emphasis on the relation of the chemistry of the sample to the fundamental mechanism of electrophoresis and the demonstration of how CE complements other methods for similar measurements. Williams, Kathryn R. J. Chem. Educ.1998, 75, 1079.

Separation Science |

Laboratory Equipment / Apparatus

Models and Molecules - A Workshop on StereoisomersRobert W. Baker, Adrian V. George, and Margaret M. HardingA molecular model workshop aimed at first year university undergraduates has been devised to illustrate the concepts of organic stereochemistry. The students build models to teach the relationship within, and between, conformational isomers, enantiomers, and diastereomers. Baker, Robert W.; George, Adrian V.; Harding, Margaret M. J. Chem. Educ.1998, 75, 853.

Molecular Properties / Structure |

Stereochemistry |

Molecular Modeling |

Enantiomers |

Diastereomers

Basic Laboratory Chemistryreviewed by Deborah McCoolBasic Laboratory Chemistry is a series of sixteen programs presenting demonstrations of many processes and experimental techniques used in the chemistry laboratory in both macroscale and microscale. Topics included in the programs are assembling macroscale and microscale apparatus, spectroscopy, chromatography, and procedures such as filtration, extraction, distillation, and titration. McCool, Deborah. J. Chem. Educ.1998, 75, 830.

Microscale Lab |

Spectroscopy |

Chromatography |

Separation Science |

Titration / Volumetric Analysis

Demonstrating Electron Transfer and Nanotechnology: A Natural Dye-Sensitized Nanocrystalline Energy ConverterGreg P. Smestad and Michael GratzelA unique solar cell fabrication procedure has been developed using natural anthocyanin dyes extracted from berries. It can be reproduced with a minimum amount of resources in order to provide an interdisciplinary approach for lower-division undergraduate students learning the basic principles of biological extraction, physical chemistry, and spectroscopy as well as environmental science and electron transfer.Smestad, Greg P.; Grtzel, Michael. J. Chem. Educ.1998, 75, 752.

Photochemistry |

Plant Chemistry |

Electrochemistry |

Atomic Properties / Structure |

Dyes / Pigments |

Nanotechnology |

Separation Science |

Spectroscopy

A Simple Streaking Device For Preparative Thin Layer ChromatographyYong J. KimIf the right tool is not available, loading a sample on a TLC plate is fairly tedious and time consuming. This article describes a procedure for making a simple and convenient streaking device from a Pasteur pipet. Kim, Yong, J. J. Chem. Educ.1998, 75, 640.

A Microscale Laboratory Heating SystemDwight KinzerA multifunctional heating system and a disposable still for use in the microscale laboratory are described. Time required for laboratory procedures is minimized. A novel microscale boiling point determination procedure is included. Kinzer, Dwight. J. Chem. Educ.1997, 74, 1333.

Laboratory Equipment / Apparatus |

Microscale Lab |

Separation Science |

Laboratory Management

Quantitative Determination of Caffeine in Beverages Using a Combined SPME-GC/MS MethodJanusz Pawliszyn, Min J. Yang, and Maureen L. OrtonSolid-phase microextraction (SPME) combined with gas chromatography/mass spectrometry (GC/MS) has been applied to the analysis of various caffeinated beverages. Unlike the current methods, this technique is solvent free and requires no pH adjustments. The simplicity of the SPME-GC/MS method lends itself to a good undergraduate laboratory practice. Pawliszyn, Janusz; Yang, Min J.; Orton, Maureen L. J. Chem. Educ.1997, 74, 1130.

HPLC for Undergraduate Introductory LaboratoriesScott A. Van Arman and Marcus W. ThomsenA set of simple HPLC separations as part of an introductory set of projects that serve as an introduction to chromatography early in the organic course; quantitative analysis has been introduced to the common separation of analgesics so that students may identify the composition of an unknown commercial tablet. Van Arman, Scott A. and Thomsen, Marcus W. J. Chem. Educ.1997, 74, 49.

Chromatography |

Quantitative Analysis |

HPLC |

Separation Science

HPLC: EARLY AND RECENT PERSPECTIVESBarry L. KargerPersonal reflections on the early days of HPLC and recent developments. HPLC has emerged from a technique that could only be imagined in the early 1960's to sales over $1.4 billion in 1994. Key to the advances has been the translation of theory to practice, in the ability to pack small particle diameter matrices of 5 mm to yield high efficiency columns. Karger, Barry L. J. Chem. Educ.1997, 74, 45.

Chromatography |

HPLC |

Separation Science

Modern Practice of Liquid Chromatography: Before and after 1971Lloyd R. SnyderA selective history (1941 through 1990) is reported of the development of high performance liquid chromatography (HPLC) from the perspective of the author. Emphasis is given to how a practical understanding of the technique emerged. Snyder, Lloyd, R. J. Chem. Educ.1997, 74, 37.

Chromatography |

HPLC |

Separation Science

Micropath Distillation ApparatusN. K. Hazra and D. MalA shortpath distillation apparatus in its inverted position can be used for microscale distillation of a liquid sample. This article describes the process.Hazra, N. K.; Mal, D. J. Chem. Educ.1996, 73, A103.

Dip Reagents for Visualization in TLCLevine, Samuel G.When employing TLC (thin layer chromatography) for colorless compounds, a step to make the spots visible after development of the plate is necessary. In this article, we show how using a dipping technique makes the visualization possible without the disadvantages of other techniques. Levine, Samuel G. J. Chem. Educ.1996, 73, A4.

Grignard Reaction of an Epoxide: A Mechanistic StudyJames A. Ciaccio, Sabrina Volpi, Ransford ClarkeUnlike most undergraduate Grignard experiments which are performed merely for the sake of illustrating a textbook reaction, this Grignard synthesis is performed to probe the reactivity of styrene oxide. Students are required to analyze their products by TLC and NMR spectroscopy (instead of just submitting them for a grade) in order to obtain the data necessary for making mechanistic conclusions. Ciaccio, James A.; Volpi, Sabrina; Clarke, Ransford. J. Chem. Educ.1996, 73, 1196.

Grignard Reagents |

Epoxides |

Thin Layer Chromatography |

NMR Spectroscopy |

Synthesis

Chromatographic Separation of Phosphoric Acid from Cola BeveragesDiego Lozano-Calero, Pilar Martìn-Palomeque, Silvia Madueño-LorguilloThe color of cola beverages interferes in the colorimetric determination of phosphoric acid. This interference is not significant if the sample is diluted sufficiently. However, a previous step where phosphoric acid is separated from the rest of the sample would be desirable. Therefore, we carried out the chromatographic separation of phosphoric acid by using an anionic exchange resin.Lozano-Calero, Diego; Martìn-Palomeque, Pilar; Madueño-Lorguillo, Silvia. J. Chem. Educ.1996, 73, 1172.

Oxygenates in Gasoline: A Versatile Experiment Using Gas ChromatographyLinda C. BrazdilAn experiment for introductory chemistry in which oxygenates are extracted from gasoline and analyzed by gas chromatography is described. The extraction of oxygenates from gasoline with water prior to analysis by gas chromatography allows for their easy identification and quantification since only the oxygenates dissolve in water. Both qualitative and quantitative versions of the experiment are described.Brazdil, Linda C. J. Chem. Educ.1996, 73, 1056.

Gas Chromatography |

Separation Science

Containment of Spray Reagents in TLC Spot DetectionJosef G. KrauseIf spraying a reagent with a power pac type device is preferred for this or some other reason, we suggest spraying the reagent inside of a twist tie-sealed, clear-plastic kitchen garbage bag.Krause, Josef G. J. Chem. Educ.1996, 73, 979.

Separation Science |

Thin Layer Chromatography |

Chromatography |

Laboratory Management

Thin-Layer Chromatography Experiments That Illustrate General Problems in ChromatographyM. Lederer, E. Leipzig-PaganiA number of chromatography experiments using cellulose thin layers and aqueous eluents are proposed to illustrate how chromatography can be used for "pattern recognition" of the inks of felt-tip pens, the principle of displacement chromatography of the constituents of the antiseptic Mercurochrome, salting-out chromatography for the separation of halides, and the impossibility to use chromatography alone as a method of identification. Lederer, M.; Leipzig-Pagani, E. J. Chem. Educ.1996, 73, 974.

Chromatography |

Dyes / Pigments |

Thin Layer Chromatography |

Separation Science

First Day in Organic LabChristine K. F. HermannThis experiment is designed to introduce students to the techniques of reflux, distillation, gas chromatography, and the determination of boiling point and melting point during one lab period. J. Chem. Educ.1996, 73, 852.

Separatory Flask and BeakerAlbert W. M. LeeSeparatory funnels are commonly used in the organic laboratory for separating organic and aqueous layers after extraction. We designed an alternative by adding a pouring sidearm to an Erlenmeyer flask or beaker that is described in this article.Lee, Albert W. M. J. Chem. Educ.1996, 73, 557.

Staining TLC Plate Using a Cotton BallAlbert W. M. Lee and Zhong ZengpeiThis article offers an alternative method of applying the staining reagents. The two common ways of application are spraying and dipping, but here we outline staining through the use of a cotton ball.Lee, Albert W. M.; Zengpei, Zhong. J. Chem. Educ.1996, 73, 358.

Using GC-MS to Determine Relative Reactivity RatiosR. Daniel Bishop, Jr.Experiment that demonstrates the use of GC-mass spectrometry in the separation and analysis of mixtures; also uses the GC-mass spectrometer to find the relative reactivity of primary, secondary, and tertiary hydrogens.Bishop, R. Daniel, Jr. J. Chem. Educ.1995, 72, 743.

Which Organic Molecule Should I Pick?Perkins, RobertExamples of questions requiring students to demonstrate their understanding of organic structures, nomenclature, isomerism, and chemical reactivity.Perkins, Robert J. Chem. Educ.1995, 72, 124.

The ABC's of Chromatography: A Colorful Demonstration.Reynolds, Robert C.; Comber, Robert N.This demonstration involves the separation of combinations of seven highly colored dyes by thin layer chromatography to help explain separation science while capturing the attention of the audience by spelling words with these dyes.Reynolds, Robert C.; Comber, Robert N. J. Chem. Educ.1994, 71, 1075.

Isolation of piperine from black pepperEpstein, William W.; Netz, David F.; Seidel, Jimmy L.A new and interesting natural product for isolation in the organic chemistry lab. This procedure also introduces students to many important instruments and procedures in organic chemistry.Epstein, William W.; Netz, David F.; Seidel, Jimmy L. J. Chem. Educ.1993, 70, 598.

Microscale distillation-Calculations and comparisons Schwartz, Marietta H.In this distillation experiment students perform both a simple and a fractional distillation using the microscale version of traditional glassware.Schwartz, Marietta H. J. Chem. Educ.1992, 69, A127.

Principle of extraction of solute by solventGuha, Prabir Kr.; Guha, RatnaAmong the applications of Nernst's distribution law, the most important and interesting one is the extraction of a substance dissolved in one solvent by another solvent, the two solvents being partially miscible or immiscible.Guha, Prabir Kr.; Guha, Ratna J. Chem. Educ.1992, 69, 73.

Solutions / Solvents |

Separation Science

The use and utility of phase scienceLaughlin, Robert G.Phase diagrams describe the phase behavior, for a particular system of mixtures spanning a particular range of system variables. One must know how to read and interpret phase diagrams in order to extract and use the information they contain.Laughlin, Robert G. J. Chem. Educ.1992, 69, 26.

Representing isomeric structuresThall, Edwin"Representing isomeric structures" is the name of a technique this author has developed to help students learn to draw molecular structures of isomers in their first organic chemistry class.Thall, Edwin J. Chem. Educ.1991, 68, 190.

Economical electrophoresis with a controlled-current power supplyHartman, David R.; Courtney, William H.Electrophoresis power supply that features a controllable current (0-90 mA, dc), the use of a common 120 V, ac power supply, and a materials cost of approximately $50.Hartman, David R.; Courtney, William H. J. Chem. Educ.1990, 67, 703.

A convenient method to recover the solvent from halogen-CCl4 mixturesSabol, Joseph E.; Kurtz, David W.An alternative to disposal and distillation which is easy to perform, allowing the solvent to be recovered and stored within one hour after the completion of the experiment is presented here.Sabol, Joseph E.; Kurtz, David W. J. Chem. Educ.1990, 67, 532.

A simple model for visualizing an organic extractionHill, John W.; McGurran, Joseph P.The authors have developed a model that provides a concrete and effective way to demonstrate the tendency of molecules of like polarity to associate with each other during extraction.Hill, John W.; McGurran, Joseph P. J. Chem. Educ.1990, 67, 303.

An automatic water trap for steam distillationRuekberg, BenThe unpleasant aspects of the water trap can be avoided with a simple, inexpensive device that renders the water trap automatically selfdraining.Ruekberg, Ben J. Chem. Educ.1990, 67, 66.

Separation Science |

Water / Water Chemistry |

Laboratory Equipment / Apparatus

Drying ethanol by azeotropic distillationMattson, Guy; Hertel, George R.The commercial process for producing absolute ethanol can be used as a basis for an unusual homework or take-home exam problem.Mattson, Guy; Hertel, George R. J. Chem. Educ.1990, 67, 46.

The interconversion of cis and trans isomersMcGinn, Clifford J.; Wheatley, William B.Trans-alkene oxides are converted to cis-alkenes on treatment with tributylphosphine, yet this reaction does not appear in most organic textbooks.McGinn, Clifford J.; Wheatley, William B. J. Chem. Educ.1989, 66, 486.

Stereochemistry |

Diastereomers |

Alkenes |

Mechanisms of Reactions

Laboratory simulations - Gel filtrationGriffith, Thomas W.102. Bits and pieces, 40. This report describes the successful use of an IBM PC program that simulates the separation and analysis of unknowns by gel filtration.Griffith, Thomas W. J. Chem. Educ.1989, 66, 407.

The separation of cobalt from nickel by anion exchange chromatography Kauffman, George B.; Adams, Matthew L.The authors have modified other experiments, using "macro" amounts of ions, and have determined the optimum conditions to produce a visually observable demonstration that illustrates several fundamental principles of the general chemistry course.Kauffman, George B.; Adams, Matthew L. J. Chem. Educ.1989, 66, 166.

Stereochemistry of cyclic hydrocarbons Perkins, Robert R.The topic of stereochemistry always poses great difficulties for many students in introductory organic chemistry. The following problems can be used as a tutorial question after having introduced the various terms associated with stereochemistry. The question requires skills at the applications level in the Bloom taxonomy.Perkins, Robert R. J. Chem. Educ.1988, 65, 860.

TLC of organic dyes in undergraduate labsSciam, Allen J.Investigation into the effectiveness of varying the solvent composition in terms of resolving the components of a mixture of dyes using thin layer chromatography.Sciam, Allen J. J. Chem. Educ.1985, 62, 361.

Models for illustrating chirality at two centersFeldman, Martin R.This note suggests common objects that can be used as models to illustrate chirality at two centers, and to introduce the concepts of diastereomers and the meso configuration.Feldman, Martin R. J. Chem. Educ.1984, 61, 1050.

High performance thin layer chromatographyCostanzo, Samuel J.Considers the various ways in which high performance has been achieved in thin layer chromatography, including the new TLC plates, sample application, plate development, and instrumental techniques.Costanzo, Samuel J. J. Chem. Educ.1984, 61, 1015.

The extraction of gold and its simulation with copperBradley, J. D.; Brand, M.; Louli, J. A. M.The simulation of the extraction of gold by the use of its analog, copper, makes it possible to capitalize on the glamor of gold without sacrificing any chemical principles.Bradley, J. D.; Brand, M.; Louli, J. A. M. J. Chem. Educ.1984, 61, 634.

Ethanol from corn: one route to gasoholMaslowsky, Edward, Jr.The experiment in this article illustrates the preparation of ethanol through the action of enzymes and yeast in whole kernel corn. The purpose is to illustrate as closely as practical the method used either industrially or on the farm to convert corn into ethanol, while a second is to illustrate distillation.Maslowsky, Edward, Jr. J. Chem. Educ.1983, 60, 752.

Production of aromatic hydrocarbons according to extractive distillation processMolinier, J.; Malmary, G.; Constrasti, J.A theme that deals with the study of the recovery of benzene from petroleum hydrocarbon mixture by means of an extractive distillation processes emerges from a pilot project that has been proposed to the graduating students.Molinier, J.; Malmary, G.; Constrasti, J. J. Chem. Educ.1983, 60, 148.

Separation Science |

Aromatic Compounds

Degas' dancers: an illustration for rotational isomersHargittai, IstvanTwo drawings by Degas provide an opportunity to introduce the concepts of staggered and eclipsed conformations of A2B-BC2 molecules in a concrete, interesting, and aesthetic way.Hargittai, Istvan J. Chem. Educ.1983, 60, 94.

Molecular Properties / Structure |

Nomenclature / Units / Symbols |

Constitutional Isomers |

Diastereomers

Structure elucidation of a natural productLetcher, Roy M.This experiment is an attempt to simulate a real-life structure elucidation problem through the isolation, characterization, and chemical transformation of an unknown naturally occurring monoterpene, with extensive use being made of spectroscopy and aided by biogenetic considerations.Letcher, Roy M. J. Chem. Educ.1983, 60, 79.

Classroom chromatographyBauer, Christopher F.A classroom demonstration in which students are used to illustrate the operation of a chromatographic column.Bauer, Christopher F. J. Chem. Educ.1982, 59, 846.

Manifold for gas chromatographyConklin, Alfred R., Jr.A manifold that allows one to operate four gas chromatographs on three tanks: one of hydrogen, one of compressed air, and one tank of carrier gas.Conklin, Alfred R., Jr. J. Chem. Educ.1982, 59, 616.

Ion exchange separation of the oxidation states of vanadiumCornelius, RichardAn experiment designed to emphasize the discrete nature of the different oxidation states of vanadium by giving students an opportunity to separate the four species by ion exchange chromatography.Cornelius, Richard J. Chem. Educ.1980, 57, 316.

Two sample applicators for chromatographyMalik, N. S. A.; Berrie, A. M. M.Designs for two thin layer chromatography applicators that can be made with a minimum of workshop facilities are described, one for small syringes and the other for larger syringes.Malik, N. S. A.; Berrie, A. M. M. J. Chem. Educ.1979, 56, 680.

Chromatography |

Laboratory Equipment / Apparatus |

Thin Layer Chromatography |

Separation Science

The rapid isolation of carotenoids from foodsMcKone, Harold T.Isolating carotene and lycopene from carrots and tomato paste without heating the organic solvents, and eliminating grinding with sand for the isolation of carotenoids from citrus fruit skins.McKone, Harold T. J. Chem. Educ.1979, 56, 676.

Selectivity and specificity in organic reactionsAult, AddisonDistinguishes between various forms of selectivity and specificity (e.g. the us of and differences between stereoselective and stereospecific).Ault, Addison J. Chem. Educ.1977, 54, 614.

Reactions |

Stereochemistry |

Diastereomers |

Enantiomers |

Nomenclature / Units / Symbols

Procedures to expedite column chromatographic separationsDorko, Ernest A.; Baker, William W.Adding a small amount of the column packing material to the mixture to be separated before evaporating its solvent and using an inflated inner tube to pressurize the column is found to expedite column chromatographic separations.Dorko, Ernest A.; Baker, William W. J. Chem. Educ.1977, 54, 564.

Separation Science |

Chromatography

Isolation of dyes for analysisLevinson, Alfred S.The use of ion exchange resin for the isolation of dyes from beverages, gelatin desserts, and other foods.Levinson, Alfred S. J. Chem. Educ.1977, 54, 460.

A sample preparation technique for column chromatographyBeller, Nicholas R.; Hilleary, Christopher J.The authors have found a simple and effective method of sample preparation for use in column chromatography which resembles the application of a sample to a thin layer chromatography plate, where the solid sample in solution is absorbed by the solid phase as the solvent evaporates.Beller, Nicholas R.; Hilleary, Christopher J. J. Chem. Educ.1976, 53, 498.

Thin Layer Chromatography |

Solutions / Solvents |

Phases / Phase Transitions / Diagrams |

Solid State Chemistry

Photooxidation of methionine. An integrated organic-analytical-biochemistry laboratory experimentLewis, Catherine; Scouten, William H.The experiments presented here familiarize the student with the organic reactions necessary to prepare the starting material; introduces the use of glass beads for immobilizing a catalyst; demonstrates the use of light and methylene blue as oxidizers; requires the implementation of an important analytical technique, thin layer chromatography; provides the student with a good example of the reactivity of one amino acid, methionine.Lewis, Catherine; Scouten, William H. J. Chem. Educ.1976, 53, 395.

Gas chromatographic analysis of gasoline. A laboratory experimentCassidy, Robert F., Jr.; Schuerch, ConradIn this experiment the authors take advantage of the high resolving power and rapidity of gas chromatography to separate some commercial gasolines into individual compounds and simple mixtures of compounds of similar volatility.Cassidy, Robert F., Jr.; Schuerch, Conrad J. Chem. Educ.1976, 53, 51.

A laboratory exercise for organic chemistrySands, Richard D.Students analyze a mixture of two unknown liquids, which as the semester progresses they are to separate, analyze, and identify.Sands, Richard D. J. Chem. Educ.1975, 52, 732.

The photoisomerization of cyclic ketones: An experiment in organic chemistryHaas, J. W., Jr.This experiment deals with parameters such as the nature of the excited state, effect of triplet quenchers on product formation, chemical structure and reaction rate and quantum yield when cyclopentanone and cyclohexanone are irradiated at 254nm. These cyclic ketones provide a variety of photolysis information in a short time span, are conveniently analyzed by gas chromatography, and are readily available at the requisite levels of purity.Haas, J. W., Jr. J. Chem. Educ.1974, 51, 346.

A simple liquid-liquid continuous extractorHolder, Richard W.For extractions of a material from a more-dense to a less-dense solvent, the setup depicted is convenient and can be constructed entirely from readily available glassware.Holder, Richard W. J. Chem. Educ.1973, 50, 639.

Filtration centrituge tubeGiese, Roger W.The tube presented is assembled from common laboratory equipment and can be employed for small scale crystallizations and filtrations under ordinary as well as low-temperature/inert-gas conditions.Giese, Roger W. J. Chem. Educ.1973, 50, 81.

The thin-layer chromatography of drugs. A laboratory experimentNeman, R. L.Students are introduced to thin layer chromatography, are provided samples known to contain alkaloids and barbiturates, separate the mixtures using tlc, determine the components of their unknowns, and calculate Rf values for the components.Neman, R. L. J. Chem. Educ.1972, 49, 834.

A multi-purpose separatory funnelKim, Young S.; Zeitlin, HarryDesign of a multi-purpose separatory funnel equipped with a Teflon stopcock in which a number of operations can be carried out conveniently.Kim, Young S.; Zeitlin, Harry J. Chem. Educ.1972, 49, 296.

Instrumental techniques compared by analysis of a reaction mixtureFairless, Billy J.; Dunn, Howard E.; Foster, Daniel O.The purpose of this experiment is to acquaint the student with how a combination of instruments (glc, ir, and nmr) can be used to separate as well as to identify each compound in a reaction mixture.Fairless, Billy J.; Dunn, Howard E.; Foster, Daniel O. J. Chem. Educ.1971, 48, 827.

Instrumental Methods |

Gas Chromatography |

Qualitative Analysis |

Separation Science

Column and thin-layer chromatography. A combined experiment for the undergraduate organic laboratoryRuppel, Irving B., Jr.; Cuneo, Frederick L.; Krause, Josef G.The authors have been using the product mixture obtained from the nitration of phenol to demonstrate the techniques of column and thin-layer chromatography with excellent results. The authors feel the experiment has several advantages over the column chromatographic experiments usually described in undergraduate laboratory manuals.Ruppel, Irving B., Jr.; Cuneo, Frederick L.; Krause, Josef G. J. Chem. Educ.1971, 48, 635.

Trimyristin from nutmegFrank, Forrest; Roberts, Theodore; Snell, Jane; Yates, Christy; Collins, JosephThe author proposes the isolation and saponification of trimytistin from nutmeg as an excellent experiment to introduce general chemistry students to laboratory techniques or for use with the organic chemistry course in which case more techniques an be introduces.Frank, Forrest; Roberts, Theodore; Snell, Jane; Yates, Christy; Collins, Joseph J. Chem. Educ.1971, 48, 255.

The preparation and isomerization of allyl thiocyanate. An organic chemistry experimentEmergon, David W.The present experiment has been devised to focus attention on two displacement reactions, one at carbon and one at sulfur and the facile allylic rearrangement of allyl thiocyanate (III) to allyl isothiocyanate (IV) which occurs during the distillation. Equations are shown in the article.Emergon, David W. J. Chem. Educ.1971, 48, 81.

Vacuum distillation experimentSchoffstall, Allen M.; Specht, James D.The primary purpose of this experiment is to provide the student with a feeling similar to that of a researcher who is attempting to separate by distillation a mixture containing a product of unknown structure for identification.Schoffstall, Allen M.; Specht, James D. J. Chem. Educ.1970, 47, 539.

An introduction to chromatographyGaucher, G. M.The object of this presentation is to serve as a preliminary practical introduction and guide to chromatography.Gaucher, G. M. J. Chem. Educ.1969, 46, 729.

Chromatography |

Separation Science |

Thin Layer Chromatography |

Gas Chromatography |

Ion Exchange

Purification of low-melting compoundsKaye, Irving AllanPresents a procedure that addresses difficulties to purification by recrystallization caused by the tendency of some low-melting compounds to precipitate from solution as oils.Kaye, Irving Allan J. Chem. Educ.1969, 46, 696.

A semi-micro filtration apparatusKocon, Richard W.An inexpensive vacuum filtration apparatus that combines the features of small surface area in the filter, rapid passage of solution through the filter, and concentration of the filtrate in a relatively small area.Kocon, Richard W. J. Chem. Educ.1969, 46, 516.

Qualitative analysis with paper chromatographyPoonia, N. S.A spot of an unknown mixture is subjected to radial development, and the circular chromatogram is divided into a number of segments used for the detection of different cations or groups of cations.Poonia, N. S. J. Chem. Educ.1967, 44, 477.

The use of talc as a tlc adsorbentWalsh, Brother Joseph M.Describes the use of talc as a thin layer chromatography adsorbent, particularly with respect to the separation of flavonoids, sugars, and proteins.Walsh, Brother Joseph M. J. Chem. Educ.1967, 44, 294.

Thin Layer Chromatography |

Chromatography |

Separation Science |

Proteins / Peptides |

Carbohydrates

Liquid-liquid extractionJoseph-Nathan, P.Describes how liquid-liquid extraction can be done using commercially available substances and an apparatus of small dimensions that still allows an experiment to be followed visually.Joseph-Nathan, P. J. Chem. Educ.1967, 44, 176.

A versatile continuous percolator-extractorCiereszko, Leon S.An apparatus that may be used either for the continuous percolation of solids or for the continuous extraction of liquids is presented.Ciereszko, Leon S. J. Chem. Educ.1966, 43, 252.

The diisopropyl ether extraction of iron(III) chlorideGuenther, William B.The diisopropyl ether extraction of iron(III) from 8 M HCl solution is a simple method of separating iron from the other components of stainless steel alloys.Guenther, William B. J. Chem. Educ.1965, 42, 277.

Separation Science |

Quantitative Analysis

Iron(III) determination using liquid-liquid extraction and colorimetryHolt, Robert L.; Easley, William K.The determination of iron(III) employing 8-hydroxyquinoline combines liquid / liquid extraction with the use of a pH meter as well as introducing the student to the formation and properties of complexes.Holt, Robert L.; Easley, William K. J. Chem. Educ.1965, 42, 276.

Resolving coordination compounds by a second order asymmetric synthesisKauffman, George B.; Sugisaka, Nobuyuki; Reid, Ian K.This experiment involves the resolution of an optically active complex cation, the trisoxalatochromate(III) ion and provides the student with an excellent introduction to the phenomenon of second order asymmetric synthesis.Kauffman, George B.; Sugisaka, Nobuyuki; Reid, Ian K. J. Chem. Educ.1964, 41, 461.

TLC separation of ink pigmentsDruding, Leonard F.The separation of inks into their component pigments was chosen for its simplicity in illustrating techniques and choice of solvent for thin layer chromatography; it also affords the student the opportunity to visually observe the course of the separation.Druding, Leonard F. J. Chem. Educ.1963, 40, 536.

Qualitative detection of Ba, Sr, and Ca ionsPariza, RichardThis short note presents a procedure for the separation of Ba++, Ca++, and Sr++ in pairs or combination of the three.Pariza, Richard J. Chem. Educ.1963, 40, 417.

A quantitative experiment with paper chromatographyFrierson, W. Joe; Marable, Nina; Bruce, BeckyA procedure developed for the separation and determination of cobalt, copper, nickel, and zinc has been combined with more recent methods for the spectrophotometric determination of cobalt and nickel and adapted to student use.Frierson, W. Joe; Marable, Nina; Bruce, Becky J. Chem. Educ.1963, 40, 408.

Simple method for determining number of theoretical platesWilliamson, A. G.Describes a method for obtaining the number of theoretical plates in a distillation column from measurements of the equilibrium temperatures at the top and bottom of the column.Williamson, A. G. J. Chem. Educ.1962, 39, 579.

Chomatographic EquipmentLewin, S. Z.Examines the following topics: selectivity in the distribution of components between two phases, chromatographic development, types of chromatographic systems, the production of counter-current flow, the scale of chromatographic separations, the components of chromatographs, the two-phase system, and containers.Lewin, S. Z. J. Chem. Educ.1961, 38, A515.

A non-cyanide separation of copper from cadmiumWaggoner, William H.A procedure has been developed for the separation of copper from cadmium that is based on the observation that thiocyanate ion will precipitate copper but not cadmium from an acidic solution.Waggoner, William H. J. Chem. Educ.1960, 37, 411.

A separation and identification experiment for elementary organic chemistry laboratoryLaughton, Paul M.The student selects a test tube containing two unknowns and is told only that they have been selected from two of three possible groups: a primary or tertiary amine, an aldehyde or ketone, and an acid or phenol. The components are to be separated, their physical properties determined, their categories assigned, and one specific derivative prepared for each.Laughton, Paul M. J. Chem. Educ.1960, 37, 133.

Separation Science |

Qualitative Analysis |

Amines / Ammonium Compounds |

Aldehydes / Ketones |

Acids / Bases |

Phenols |

Physical Properties |

Synthesis

The separation of arsenic in qualitative analysisBoyd, Clifford C.; Easley, William K.A separation of arsenic as As(III) has been developed based upon the observation that As(III) is extracted selectively from hydrochloric acid solution of the common cations encountered in the usual qualitative analysis scheme.Boyd, Clifford C.; Easley, William K. J. Chem. Educ.1959, 36, 384.

Separation of copper(II) from cadmium (II) in qualitative analysisBoyd, Clifford C.; Easley, William K.This procedure is based on the observation that copper(II) ion is extracted selectively from solutions containing copper(II) and cadmium(II) by a solution of 8-hydroxyquinoline in chloroform.Boyd, Clifford C.; Easley, William K. J. Chem. Educ.1958, 35, 406.

Use of ion exchange resins with nonaqueous and mixed solventsBonner, O. D.This review examines some of the recent developments in the use of synthetic ion exchangers for three types of separations: the separation of ionic substances in nonaqueous or mixed solvents, the separation of nonionic substances in nonaqueous or mixed solutions, and the separation of ionic from nonionic materials in solution.Bonner, O. D. J. Chem. Educ.1957, 34, 174.

Ion Exchange |

Separation Science |

Solutions / Solvents

Apparatus for the triple distillation of mercuryJoncich, M. J.; Alley, C. A.; Kowaka, M.The rising cost of mercury coupled with the extensive use of this element in a variety of laboratory applications emphasizes the need for an efficient apparatus for purification.Joncich, M. J.; Alley, C. A.; Kowaka, M. J. Chem. Educ.1956, 33, 607.

Student experiments on derivatives of 1,2-diphenylethaneFieser, Louis F.Johannes Thiele's classical demonstration of 1,4-addition by reductive acetylation of benzil is used to present a number of interesting theoretical points and an opportunity to separate cis- and trans- isomers through chromatography.Fieser, Louis F. J. Chem. Educ.1954, 31, 291.

A visual demonstration of fractional distillationOsburn, James O.Describes the design of a glass bubble-cap column, a glass-packed column, and an equilibrium diagram for an engineering department open-house.Osburn, James O. J. Chem. Educ.1953, 30, 412.

A convenient apparatus for the distillation of solidsBarkley, Lloyd B.; Sneed, James K.; McGrath, Thomas F.; Levine, RobertThis apparatus is designed to overcome common difficulties in the distillation of solids or mixtures of solids.Barkley, Lloyd B.; Sneed, James K.; McGrath, Thomas F.; Levine, Robert J. Chem. Educ.1953, 30, 115.

A lecture demonstration of ion exchangeSmith, James BoydThis paper presents specific procedures for three experiments that may be employed for lecture demonstrations of ion exchange.Smith, James Boyd J. Chem. Educ.1952, 29, 292.

Ion Exchange |

Separation Science

A continuous ether-extraction apparatusHolliman, F. G.The apparatus presented has been constructed to provide both speed of assembly and versatility in respect of volume of solution being extracted.Holliman, F. G. J. Chem. Educ.1952, 29, 96.